Deadlines are a natural part of our work lives, and they can be both frustrating and productive. The planning fallacy, which is our tendency to underestimate how long tasks take to complete, often leads us into missing deadlines. This bias affects our thinking as the deadline approaches, making it more realistic, but also causing us to attribute failing to meet deadlines to external factors rather than our own inability to plan effectively. To overcome this bias and make deadlines work for us, we can front-load our workload, give ourselves a buffer, commit to public deadlines, and use automated reminders of upcoming due dates. By understanding the planning fallacy and implementing these strategies, we can improve our productivity and meet our deadlines with more confidence.